#------------------------------------------------------------------------------
#$Date: 2025-11-29 18:50:01 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303559 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/49/7134992.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134992
loop_
_publ_author_name
'Zhai, Jing-Jing'
'Lou, Shao-Jie'
'Zhang, Xiao-Xiao'
'Lan, Qiu-Yi'
'Jing, Cheng-Cheng'
'Mao, Yang-Jie'
'Wang, Yi-Feng'
'Chu, Ming-Ming'
'Xu, Dan-Qian'
_publ_section_title
;
 Remote asymmetric conjugate addition of naphthoquinone methides:
 constructing adjacent tertiary-quaternary carbon stereocenters.
;
_journal_issue                   85
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16644
_journal_page_last               16647
_journal_paper_doi               10.1039/d5cc03265b
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H20 Br O4, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C28.5 H21 Br Cl O4'
_chemical_formula_weight         542.81
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                106.141(2)
_cell_angle_beta                 96.303(2)
_cell_angle_gamma                107.287(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0354(5)
_cell_length_b                   11.1067(6)
_cell_length_c                   13.6619(8)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.41
_cell_volume                     1229.51(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11336
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.032
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0993 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8872.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         7613
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0359P)²+0.9032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.353
_reflns_Friedel_fraction_full    0.372
_reflns_Friedel_fraction_max     0.351
_reflns_number_gt                6455
_reflns_number_total             7613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc03265b2.cif
_cod_data_source_block           221021li_lidz173796_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134992--7134994.cif.
;
_cod_original_formula_sum        'C28.50 H21 Br Cl O4'
_cod_database_code               7134992
_shelx_shelxl_version_number     2019/2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.839
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B)
2.c Aromatic/amide H refined with riding coordinates:
 C54(H54), C45(H45), C10(H10), C26(H26), C13(H13), C49(H49), C14(H14),
 C33(H33), C5(H5), C31(H31), C21(H21), C41(H41), C44(H44), C15(H15), C52(H52),
 C42(H42), C51(H51), C23(H23), C8(H8A), C7(H7), C17(H17), C35(H35), C43(H43),
 C30(H30), C36(H36), C2(H2), C3(H3), C24(H24), C38(H38), C16(H16)
2.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
loop_
_space_group_symop_operation_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br -0.08411(7) 1.18949(6) 0.29367(6) 0.0486(2) Uani 1 1 d . . . . .
Br1 Br 0.86382(10) -0.19012(7) 0.94644(6) 0.0667(3) Uani 1 1 d . . . . .
Cl2 Cl 1.1762(3) 0.8222(3) 0.7048(3) 0.0924(9) Uani 1 1 d . . . . .
Cl1 Cl 1.3328(4) 1.0907(3) 0.8477(3) 0.1053(10) Uani 1 1 d . . . . .
O5 O 0.2165(5) 0.8225(4) 0.1003(3) 0.0312(8) Uani 1 1 d . . . . .
O6 O 0.4702(5) 0.7402(4) 0.1739(4) 0.0367(10) Uani 1 1 d . . . . .
O1 O 0.9223(6) 0.0512(4) 0.6236(3) 0.0390(10) Uani 1 1 d . . . . .
O2 O 0.6607(5) 0.1253(4) 0.5178(3) 0.0390(10) Uani 1 1 d . . . . .
O7 O 0.5030(5) 0.8152(4) 0.3455(4) 0.0382(10) Uani 1 1 d . . . . .
O8 O 0.5101(5) 0.0622(4) 0.3038(4) 0.0389(10) Uani 1 1 d . . . . .
H8 H 0.535841 0.070611 0.365481 0.058 Uiso 1 1 calc R U . . .
O4 O 0.5254(6) 0.8382(5) 0.5552(4) 0.0484(12) Uani 1 1 d . . . . .
H4 H 0.540373 0.842405 0.497922 0.073 Uiso 1 1 calc R U . . .
O3 O 0.5251(5) 0.1475(4) 0.6460(3) 0.0400(10) Uani 1 1 d . . . . .
C54 C 0.0566(7) 0.9919(5) 0.2352(5) 0.0282(11) Uani 1 1 d . . . . .
H54 H 0.064479 1.015094 0.175119 0.034 Uiso 1 1 calc R U . . .
C55 C 0.1131(6) 0.8929(5) 0.2532(4) 0.0251(11) Uani 1 1 d . . . . .
C53 C -0.0100(6) 1.0519(6) 0.3103(5) 0.0299(13) Uani 1 1 d . . . . .
C50 C 0.1022(6) 0.8562(5) 0.3404(4) 0.0260(11) Uani 1 1 d . . . . .
C45 C -0.1085(7) 0.4692(6) 0.1970(6) 0.0330(14) Uani 1 1 d . . . . .
H45 H -0.056374 0.451657 0.251213 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6988(7) 0.7083(6) 0.5347(5) 0.0334(13) Uani 1 1 d . . . . .
H10 H 0.741889 0.745538 0.486616 0.040 Uiso 1 1 calc R U . . .
C26 C 0.8627(8) -0.0374(6) 0.8125(5) 0.0354(13) Uani 1 1 d . . . . .
H26 H 0.894519 -0.099850 0.767230 0.042 Uiso 1 1 calc R U . . .
C39 C 0.1595(6) 0.5776(5) 0.1572(5) 0.0279(12) Uani 1 1 d . . . . .
H39 H 0.188441 0.585566 0.091651 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7539(7) 0.6138(5) 0.5635(5) 0.0297(12) Uani 1 1 d . . . . .
C56 C 0.1918(6) 0.8175(5) 0.1844(4) 0.0245(11) Uani 1 1 d . . . . .
C27 C 0.8408(7) 0.0716(5) 0.7873(4) 0.0286(12) Uani 1 1 d . . . . .
C13 C 1.1141(7) 0.5332(6) 0.8124(5) 0.0357(13) Uani 1 1 d . . . . .
H13 H 1.043179 0.577247 0.803916 0.043 Uiso 1 1 calc R U . . .
C40 C -0.0199(6) 0.5324(5) 0.1361(5) 0.0281(12) Uani 1 1 d . . . . .
C1 C 0.5818(7) 0.7451(6) 0.5776(5) 0.0349(13) Uani 1 1 d . . . . .
C32 C 0.3518(7) 0.3722(6) 0.2814(5) 0.0364(14) Uani 1 1 d . . . . .
C18 C 0.8065(7) 0.2245(5) 0.6954(4) 0.0291(12) Uani 1 1 d . . . . .
C28 C 0.8663(7) 0.1039(5) 0.6920(5) 0.0298(12) Uani 1 1 d . . . . .
C19 C 0.6563(7) 0.1612(5) 0.6099(5) 0.0304(12) Uani 1 1 d . . . . .
C49 C 0.1752(7) 0.7496(6) 0.3403(5) 0.0323(13) Uani 1 1 d . . . . .
H49 H 0.181730 0.709678 0.391343 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6912(7) 0.5613(5) 0.6397(5) 0.0318(12) Uani 1 1 d . . . . .
C14 C 1.2487(8) 0.5976(7) 0.8911(5) 0.0423(15) Uani 1 1 d . . . . .
H14 H 1.266739 0.683199 0.935588 0.051 Uiso 1 1 calc R U . . .
C33 C 0.2945(7) 0.4786(6) 0.2694(6) 0.0391(14) Uani 1 1 d . . . . .
H33 H 0.311508 0.552963 0.327238 0.047 Uiso 1 1 calc R U . . .
C46 C 0.2363(6) 0.7212(5) 0.2386(4) 0.0253(11) Uani 1 1 d . . . . .
C47 C 0.4189(6) 0.7646(5) 0.2615(5) 0.0294(12) Uani 1 1 d . . . . .
C22 C 0.7919(7) 0.1647(6) 0.8526(5) 0.0307(12) Uani 1 1 d . . . . .
C37 C 0.3257(6) 0.2634(6) 0.1923(5) 0.0324(13) Uani 1 1 d . . . . .
C5 C 0.7480(7) 0.4678(6) 0.6697(5) 0.0313(12) Uani 1 1 d . . . . .
H5 H 0.706513 0.434379 0.719963 0.038 Uiso 1 1 calc R U . . .
C31 C 0.4346(8) 0.3815(6) 0.3762(5) 0.0417(15) Uani 1 1 d . . . . .
H31 H 0.453389 0.455581 0.434590 0.050 Uiso 1 1 calc R U . . .
C11 C 0.9310(7) 0.3315(5) 0.6615(4) 0.0295(12) Uani 1 1 d . . . . .
H11 H 0.960784 0.281792 0.600132 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7793(7) 0.2710(5) 0.8075(5) 0.0308(12) Uani 1 1 d . . . . .
H21 H 0.759369 0.348301 0.840018 0.037 Uiso 1 1 calc R U . . .
C41 C -0.1012(7) 0.5499(6) 0.0526(5) 0.0315(13) Uani 1 1 d . . . . .
H41 H -0.044907 0.588671 0.009590 0.038 Uiso 1 1 calc R U . . .
C44 C -0.2719(7) 0.4323(6) 0.1781(6) 0.0420(16) Uani 1 1 d . . . . .
H44 H -0.328590 0.394281 0.221347 0.050 Uiso 1 1 calc R U . . .
C15 C 1.3559(8) 0.5340(7) 0.9033(6) 0.0472(17) Uani 1 1 d . . . . .
H15 H 1.446256 0.576547 0.956262 0.057 Uiso 1 1 calc R U . . .
C34 C 0.2192(6) 0.4712(5) 0.1781(5) 0.0331(14) Uani 1 1 d . . . . .
C52 C -0.0266(7) 1.0145(6) 0.3996(5) 0.0353(13) Uani 1 1 d . . . . .
H52 H -0.074862 1.055918 0.448850 0.042 Uiso 1 1 calc R U . . .
C42 C -0.2646(7) 0.5111(6) 0.0316(6) 0.0387(14) Uani 1 1 d . . . . .
H42 H -0.316578 0.524529 -0.024933 0.046 Uiso 1 1 calc R U . . .
C51 C 0.0288(7) 0.9161(6) 0.4144(5) 0.0343(13) Uani 1 1 d . . . . .
H51 H 0.017149 0.890154 0.473024 0.041 Uiso 1 1 calc R U . . .
C23 C 0.7636(8) 0.1525(6) 0.9486(5) 0.0388(14) Uani 1 1 d . . . . .
H23 H 0.731486 0.214518 0.994128 0.047 Uiso 1 1 calc R U . . .
C8 C 0.8723(7) 0.5685(6) 0.5206(5) 0.0381(14) Uani 1 1 d . . . . .
H8A H 0.915710 0.601055 0.470480 0.046 Uiso 1 1 calc R U . . .
C29 C 0.4626(7) 0.1669(6) 0.2959(5) 0.0360(14) Uani 1 1 d . . . . .
C7 C 0.9232(8) 0.4783(6) 0.5518(5) 0.0372(14) Uani 1 1 d . . . . .
H7 H 1.000722 0.450764 0.522582 0.045 Uiso 1 1 calc R U . . .
C12 C 1.0824(7) 0.4051(5) 0.7459(5) 0.0294(12) Uani 1 1 d . . . . .
C17 C 1.1945(8) 0.3445(7) 0.7583(6) 0.0432(16) Uani 1 1 d . . . . .
H17 H 1.179265 0.259927 0.712986 0.052 Uiso 1 1 calc R U . . .
C35 C 0.1892(7) 0.3534(6) 0.0885(5) 0.0360(13) Uani 1 1 d . . . . .
H35 H 0.133124 0.346418 0.024673 0.043 Uiso 1 1 calc R U . . .
C43 C -0.3517(8) 0.4525(7) 0.0935(6) 0.0434(17) Uani 1 1 d . . . . .
H43 H -0.461667 0.426798 0.079252 0.052 Uiso 1 1 calc R U . . .
C25 C 0.8352(9) -0.0465(6) 0.9057(5) 0.0399(15) Uani 1 1 d . . . . .
C6 C 0.8601(7) 0.4256(5) 0.6281(5) 0.0300(12) Uani 1 1 d . . . . .
C30 C 0.4892(8) 0.2800(6) 0.3834(6) 0.0435(16) Uani 1 1 d . . . . .
H30 H 0.544640 0.286371 0.447285 0.052 Uiso 1 1 calc R U . . .
C36 C 0.2418(7) 0.2534(6) 0.0967(5) 0.0356(14) Uani 1 1 d . . . . .
H36 H 0.221958 0.178461 0.038734 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5173(9) 0.6914(6) 0.6512(6) 0.0444(16) Uani 1 1 d . . . . .
H2 H 0.438146 0.717281 0.679519 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5692(8) 0.6022(7) 0.6817(5) 0.0446(16) Uani 1 1 d . . . . .
H3 H 0.524942 0.567202 0.730517 0.054 Uiso 1 1 calc R U . . .
C48 C 0.6418(7) 0.7924(8) 0.1865(7) 0.0542(19) Uani 1 1 d . . . . .
H48A H 0.669657 0.765746 0.120032 0.081 Uiso 1 1 calc R U . . .
H48B H 0.690228 0.757814 0.233260 0.081 Uiso 1 1 calc R U . . .
H48C H 0.678522 0.888030 0.214615 0.081 Uiso 1 1 calc R U . . .
C24 C 0.7846(9) 0.0455(7) 0.9741(5) 0.0484(17) Uani 1 1 d . . . . .
H24 H 0.765075 0.034585 1.037089 0.058 Uiso 1 1 calc R U . . .
C38 C 0.3856(7) 0.1566(6) 0.2008(6) 0.0404(15) Uani 1 1 d . . . . .
H38 H 0.371256 0.083565 0.142499 0.048 Uiso 1 1 calc R U . . .
C16 C 1.3295(8) 0.4095(7) 0.8381(6) 0.0479(17) Uani 1 1 d . . . . .
H16 H 1.402089 0.366963 0.846611 0.057 Uiso 1 1 calc R U . . .
C20 C 0.3765(8) 0.0858(7) 0.5697(6) 0.0509(18) Uani 1 1 d . . . . .
H20A H 0.377879 0.006068 0.519750 0.076 Uiso 1 1 calc R U . . .
H20B H 0.362970 0.146800 0.534554 0.076 Uiso 1 1 calc R U . . .
H20C H 0.290274 0.063572 0.604226 0.076 Uiso 1 1 calc R U . . .
C57 C 1.3522(16) 0.9409(11) 0.7943(13) 0.120(5) Uani 1 1 d . . . . .
H57A H 1.377954 0.906463 0.849357 0.144 Uiso 1 1 calc R U . . .
H57B H 1.439414 0.952466 0.758168 0.144 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C47 O6 C48 114.7(5) . . ?
C29 O8 H8 109.5 . . ?
C1 O4 H4 109.5 . . ?
C19 O3 C20 116.9(5) . . ?
C55 C54 H54 121.7 . . ?
C53 C54 H54 121.7 . . ?
C53 C54 C55 116.6(5) . . ?
C54 C55 C56 126.0(5) . . ?
C50 C55 C54 123.0(5) . . ?
C50 C55 C56 111.0(4) . . ?
C54 C53 Br2 119.2(4) . . ?
C54 C53 C52 122.0(5) . . ?
C52 C53 Br2 118.8(5) . . ?
C55 C50 C49 111.7(5) . . ?
C55 C50 C51 119.2(5) . . ?
C51 C50 C49 129.1(5) . . ?
C40 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C44 C45 C40 121.2(6) . . ?
C9 C10 H10 120.0 . . ?
C1 C10 H10 120.0 . . ?
C1 C10 C9 120.1(5) . . ?
C27 C26 H26 121.8 . . ?
C25 C26 H26 121.8 . . ?
C25 C26 C27 116.5(6) . . ?
C40 C39 H39 105.5 . . ?
C40 C39 C46 111.6(5) . . ?
C40 C39 C34 111.4(4) . . ?
C46 C39 H39 105.5 . . ?
C34 C39 H39 105.5 . . ?
C34 C39 C46 116.4(5) . . ?
C10 C9 C4 119.4(5) . . ?
C10 C9 C8 123.3(5) . . ?
C4 C9 C8 117.3(5) . . ?
O5 C56 C55 128.2(5) . . ?
O5 C56 C46 124.5(5) . . ?
C55 C56 C46 107.3(4) . . ?
C26 C27 C28 126.4(6) . . ?
C22 C27 C26 122.9(5) . . ?
C22 C27 C28 110.7(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.7(6) . . ?
C45 C40 C39 122.3(5) . . ?
C41 C40 C45 118.0(5) . . ?
C41 C40 C39 119.7(5) . . ?
O4 C1 C10 123.2(5) . . ?
O4 C1 C2 116.0(6) . . ?
C10 C1 C2 120.7(5) . . ?
C37 C32 C33 117.3(6) . . ?
C31 C32 C33 121.5(6) . . ?
C31 C32 C37 121.1(6) . . ?
C28 C18 C11 109.3(5) . . ?
C19 C18 C28 103.1(4) . . ?
C19 C18 C11 107.7(4) . . ?
C19 C18 C21 115.0(5) . . ?
C21 C18 C28 104.0(4) . . ?
C21 C18 C11 116.6(5) . . ?
O1 C28 C27 128.0(5) . . ?
O1 C28 C18 125.4(5) . . ?
C27 C28 C18 106.6(5) . . ?
O2 C19 O3 124.6(5) . . ?
O2 C19 C18 122.0(6) . . ?
O3 C19 C18 113.4(5) . . ?
C50 C49 H49 127.0 . . ?
C50 C49 C46 105.9(4) . . ?
C46 C49 H49 127.0 . . ?
C9 C4 C5 119.4(5) . . ?
C9 C4 C3 118.4(5) . . ?
C5 C4 C3 122.1(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(7) . . ?
C15 C14 H14 120.2 . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.4(6) . . ?
C34 C33 H33 119.3 . . ?
C39 C46 C56 105.9(4) . . ?
C49 C46 C39 117.5(4) . . ?
C49 C46 C56 104.0(4) . . ?
C49 C46 C47 110.9(5) . . ?
C47 C46 C39 111.1(4) . . ?
C47 C46 C56 106.5(4) . . ?
O6 C47 C46 110.5(5) . . ?
O7 C47 O6 124.1(5) . . ?
O7 C47 C46 125.5(6) . . ?
C27 C22 C21 112.0(5) . . ?
C27 C22 C23 119.4(5) . . ?
C23 C22 C21 128.5(5) . . ?
C32 C37 C38 118.8(5) . . ?
C36 C37 C32 121.4(6) . . ?
C36 C37 C38 119.8(6) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 C4 122.5(5) . . ?
C6 C5 H5 118.7 . . ?
C32 C31 H31 120.2 . . ?
C30 C31 C32 119.6(6) . . ?
C30 C31 H31 120.2 . . ?
C18 C11 H11 106.7 . . ?
C12 C11 C18 111.0(4) . . ?
C12 C11 H11 106.7 . . ?
C6 C11 C18 112.4(5) . . ?
C6 C11 H11 106.7 . . ?
C6 C11 C12 112.8(5) . . ?
C18 C21 H21 127.3 . . ?
C22 C21 C18 105.4(4) . . ?
C22 C21 H21 127.3 . . ?
C40 C41 H41 119.4 . . ?
C40 C41 C42 121.3(6) . . ?
C42 C41 H41 119.4 . . ?
C45 C44 H44 120.2 . . ?
C45 C44 C43 119.6(6) . . ?
C43 C44 H44 120.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
C33 C34 C39 125.3(6) . . ?
C33 C34 C35 119.2(5) . . ?
C35 C34 C39 115.5(5) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 C53 119.9(6) . . ?
C51 C52 H52 120.0 . . ?
C41 C42 H42 119.6 . . ?
C43 C42 C41 120.8(6) . . ?
C43 C42 H42 119.6 . . ?
C50 C51 H51 120.4 . . ?
C52 C51 C50 119.3(5) . . ?
C52 C51 H51 120.4 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 C22 118.2(6) . . ?
C24 C23 H23 120.9 . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8A 119.4 . . ?
O8 C29 C30 121.5(5) . . ?
C38 C29 O8 117.9(6) . . ?
C38 C29 C30 120.6(5) . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C6 121.4(6) . . ?
C6 C7 H7 119.3 . . ?
C13 C12 C11 121.9(5) . . ?
C13 C12 C17 117.5(6) . . ?
C17 C12 C11 120.6(5) . . ?
C12 C17 H17 119.7 . . ?
C12 C17 C16 120.5(7) . . ?
C16 C17 H17 119.7 . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 120.9(6) . . ?
C36 C35 H35 119.5 . . ?
C44 C43 H43 120.5 . . ?
C42 C43 C44 119.0(6) . . ?
C42 C43 H43 120.5 . . ?
C26 C25 Br1 119.2(5) . . ?
C26 C25 C24 122.5(6) . . ?
C24 C25 Br1 118.2(5) . . ?
C5 C6 C11 124.6(5) . . ?
C5 C6 C7 118.1(5) . . ?
C7 C6 C11 117.2(5) . . ?
C31 C30 C29 121.3(6) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C37 C36 H36 120.1 . . ?
C35 C36 C37 119.7(6) . . ?
C35 C36 H36 120.1 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.6 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3 119.7 . . ?
O6 C48 H48A 109.5 . . ?
O6 C48 H48B 109.5 . . ?
O6 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C23 C24 C25 120.5(6) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C37 C38 H38 120.7 . . ?
C29 C38 C37 118.6(6) . . ?
C29 C38 H38 120.7 . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl2 C57 H57A 109.1 . . ?
Cl2 C57 H57B 109.1 . . ?
Cl1 C57 Cl2 112.4(7) . . ?
Cl1 C57 H57A 109.1 . . ?
Cl1 C57 H57B 109.1 . . ?
H57A C57 H57B 107.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C53 1.898(6) . ?
Br1 C25 1.906(6) . ?
Cl2 C57 1.787(13) . ?
Cl1 C57 1.691(11) . ?
O5 C56 1.206(7) . ?
O6 C47 1.317(7) . ?
O6 C48 1.456(7) . ?
O1 C28 1.202(7) . ?
O2 C19 1.218(8) . ?
O7 C47 1.186(7) . ?
O8 H8 0.8200 . ?
O8 C29 1.380(6) . ?
O4 H4 0.8200 . ?
O4 C1 1.370(6) . ?
O3 C19 1.317(7) . ?
O3 C20 1.452(8) . ?
C54 H54 0.9300 . ?
C54 C55 1.410(7) . ?
C54 C53 1.361(9) . ?
C55 C50 1.366(7) . ?
C55 C56 1.468(8) . ?
C53 C52 1.403(9) . ?
C50 C49 1.516(7) . ?
C50 C51 1.392(8) . ?
C45 H45 0.9300 . ?
C45 C40 1.402(8) . ?
C45 C44 1.383(9) . ?
C10 H10 0.9300 . ?
C10 C9 1.415(7) . ?
C10 C1 1.375(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.408(7) . ?
C26 C25 1.349(9) . ?
C39 H39 0.9800 . ?
C39 C40 1.516(7) . ?
C39 C46 1.564(8) . ?
C39 C34 1.517(7) . ?
C9 C4 1.419(8) . ?
C9 C8 1.427(9) . ?
C56 C46 1.576(6) . ?
C27 C28 1.468(8) . ?
C27 C22 1.380(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(9) . ?
C13 C12 1.383(8) . ?
C40 C41 1.380(8) . ?
C1 C2 1.401(9) . ?
C32 C33 1.464(8) . ?
C32 C37 1.396(9) . ?
C32 C31 1.383(9) . ?
C18 C28 1.578(7) . ?
C18 C19 1.526(8) . ?
C18 C11 1.587(8) . ?
C18 C21 1.546(8) . ?
C49 H49 0.9300 . ?
C49 C46 1.538(8) . ?
C4 C5 1.420(7) . ?
C4 C3 1.430(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.323(9) . ?
C46 C47 1.543(7) . ?
C22 C21 1.502(7) . ?
C22 C23 1.399(8) . ?
C37 C36 1.394(8) . ?
C37 C38 1.469(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(8) . ?
C31 H31 0.9300 . ?
C31 C30 1.381(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.528(8) . ?
C11 C6 1.519(7) . ?
C21 H21 0.9300 . ?
C41 H41 0.9300 . ?
C41 C42 1.381(8) . ?
C44 H44 0.9300 . ?
C44 C43 1.402(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.355(10) . ?
C34 C35 1.452(9) . ?
C52 H52 0.9300 . ?
C52 C51 1.383(9) . ?
C42 H42 0.9300 . ?
C42 C43 1.381(10) . ?
C51 H51 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.385(9) . ?
C8 H8A 0.9300 . ?
C8 C7 1.366(8) . ?
C29 C30 1.410(10) . ?
C29 C38 1.363(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.424(8) . ?
C12 C17 1.393(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.394(10) . ?
C35 H35 0.9300 . ?
C35 C36 1.358(8) . ?
C43 H43 0.9300 . ?
C25 C24 1.402(10) . ?
C30 H30 0.9300 . ?
C36 H36 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.356(8) . ?
C3 H3 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C24 H24 0.9300 . ?
C38 H38 0.9300 . ?
C16 H16 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C53 C52 C51 -178.9(4) . . . . ?
Br1 C25 C24 C23 179.3(5) . . . . ?
O5 C56 C46 C39 -53.5(6) . . . . ?
O5 C56 C46 C49 -177.9(5) . . . . ?
O5 C56 C46 C47 64.9(6) . . . . ?
O8 C29 C30 C31 -176.8(6) . . . . ?
O8 C29 C38 C37 176.4(5) . . . . ?
O4 C1 C2 C3 -177.6(6) . . . . ?
C54 C55 C50 C49 -178.9(5) . . . . ?
C54 C55 C50 C51 1.6(8) . . . . ?
C54 C55 C56 O5 -3.0(9) . . . . ?
C54 C55 C56 C46 178.8(5) . . . . ?
C54 C53 C52 C51 1.5(9) . . . . ?
C55 C54 C53 Br2 178.4(4) . . . . ?
C55 C54 C53 C52 -2.0(8) . . . . ?
C55 C50 C49 C46 -0.1(6) . . . . ?
C55 C50 C51 C52 -2.2(8) . . . . ?
C55 C56 C46 C39 124.8(4) . . . . ?
C55 C56 C46 C49 0.4(5) . . . . ?
C55 C56 C46 C47 -116.8(5) . . . . ?
C53 C54 C55 C50 0.5(8) . . . . ?
C53 C54 C55 C56 -178.7(5) . . . . ?
C53 C52 C51 C50 0.7(9) . . . . ?
C50 C55 C56 O5 177.8(5) . . . . ?
C50 C55 C56 C46 -0.5(6) . . . . ?
C50 C49 C46 C39 -116.8(5) . . . . ?
C50 C49 C46 C56 -0.2(5) . . . . ?
C50 C49 C46 C47 114.0(5) . . . . ?
C45 C40 C41 C42 2.4(10) . . . . ?
C45 C44 C43 C42 -1.1(10) . . . . ?
C10 C9 C4 C5 -179.1(5) . . . . ?
C10 C9 C4 C3 2.5(8) . . . . ?
C10 C9 C8 C7 179.2(6) . . . . ?
C10 C1 C2 C3 0.1(10) . . . . ?
C26 C27 C28 O1 -6.9(10) . . . . ?
C26 C27 C28 C18 173.5(5) . . . . ?
C26 C27 C22 C21 179.5(5) . . . . ?
C26 C27 C22 C23 0.5(9) . . . . ?
C26 C25 C24 C23 -1.2(11) . . . . ?
C39 C40 C41 C42 -179.4(6) . . . . ?
C39 C46 C47 O6 47.6(6) . . . . ?
C39 C46 C47 O7 -133.7(5) . . . . ?
C39 C34 C35 C36 177.7(5) . . . . ?
C9 C10 C1 O4 178.4(6) . . . . ?
C9 C10 C1 C2 1.0(9) . . . . ?
C9 C4 C5 C6 -0.3(9) . . . . ?
C9 C4 C3 C2 -1.5(10) . . . . ?
C9 C8 C7 C6 0.1(10) . . . . ?
C56 C55 C50 C49 0.4(6) . . . . ?
C56 C55 C50 C51 -179.1(5) . . . . ?
C56 C46 C47 O6 -67.3(5) . . . . ?
C56 C46 C47 O7 111.5(6) . . . . ?
C27 C26 C25 Br1 -179.4(5) . . . . ?
C27 C26 C25 C24 1.1(10) . . . . ?
C27 C22 C21 C18 7.1(7) . . . . ?
C27 C22 C23 C24 -0.6(9) . . . . ?
C13 C14 C15 C16 0.3(10) . . . . ?
C13 C12 C17 C16 2.9(9) . . . . ?
C40 C45 C44 C43 3.1(10) . . . . ?
C40 C39 C46 C56 -66.2(6) . . . . ?
C40 C39 C46 C49 49.4(6) . . . . ?
C40 C39 C46 C47 178.6(5) . . . . ?
C40 C39 C34 C33 -109.8(7) . . . . ?
C40 C39 C34 C35 70.4(7) . . . . ?
C40 C41 C42 C43 -0.4(10) . . . . ?
C1 C10 C9 C4 -2.2(8) . . . . ?
C1 C10 C9 C8 178.6(6) . . . . ?
C1 C2 C3 C4 0.2(11) . . . . ?
C32 C33 C34 C39 -178.2(5) . . . . ?
C32 C33 C34 C35 1.6(9) . . . . ?
C32 C37 C36 C35 2.6(9) . . . . ?
C32 C37 C38 C29 0.9(8) . . . . ?
C32 C31 C30 C29 0.2(10) . . . . ?
C18 C11 C12 C13 -102.8(6) . . . . ?
C18 C11 C12 C17 77.4(7) . . . . ?
C18 C11 C6 C5 33.8(8) . . . . ?
C18 C11 C6 C7 -149.9(5) . . . . ?
C28 C27 C22 C21 0.0(7) . . . . ?
C28 C27 C22 C23 -179.0(5) . . . . ?
C28 C18 C19 O2 -70.7(6) . . . . ?
C28 C18 C19 O3 108.0(5) . . . . ?
C28 C18 C11 C12 -71.6(6) . . . . ?
C28 C18 C11 C6 161.0(5) . . . . ?
C28 C18 C21 C22 -10.6(6) . . . . ?
C19 C18 C28 O1 70.7(7) . . . . ?
C19 C18 C28 C27 -109.6(5) . . . . ?
C19 C18 C11 C12 177.1(5) . . . . ?
C19 C18 C11 C6 49.7(6) . . . . ?
C19 C18 C21 C22 101.4(5) . . . . ?
C49 C50 C51 C52 178.4(5) . . . . ?
C49 C46 C47 O6 -179.8(4) . . . . ?
C49 C46 C47 O7 -1.1(7) . . . . ?
C4 C9 C8 C7 0.0(9) . . . . ?
C4 C5 C6 C11 176.7(5) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
C14 C13 C12 C11 177.7(6) . . . . ?
C14 C13 C12 C17 -2.6(9) . . . . ?
C14 C15 C16 C17 0.0(11) . . . . ?
C33 C32 C37 C36 -3.0(8) . . . . ?
C33 C32 C37 C38 178.3(5) . . . . ?
C33 C32 C31 C30 -178.7(6) . . . . ?
C33 C34 C35 C36 -2.1(9) . . . . ?
C46 C39 C40 C45 -87.1(6) . . . . ?
C46 C39 C40 C41 94.7(6) . . . . ?
C46 C39 C34 C33 19.6(8) . . . . ?
C46 C39 C34 C35 -160.2(5) . . . . ?
C22 C27 C28 O1 172.7(6) . . . . ?
C22 C27 C28 C18 -7.0(6) . . . . ?
C22 C23 C24 C25 0.9(10) . . . . ?
C37 C32 C33 C34 0.9(9) . . . . ?
C37 C32 C31 C30 -1.6(10) . . . . ?
C5 C4 C3 C2 -179.9(7) . . . . ?
C31 C32 C33 C34 178.1(6) . . . . ?
C31 C32 C37 C36 179.8(6) . . . . ?
C31 C32 C37 C38 1.0(9) . . . . ?
C11 C18 C28 O1 -43.6(8) . . . . ?
C11 C18 C28 C27 136.1(5) . . . . ?
C11 C18 C19 O2 44.9(7) . . . . ?
C11 C18 C19 O3 -136.4(5) . . . . ?
C11 C18 C21 C22 -131.0(5) . . . . ?
C11 C12 C17 C16 -177.4(6) . . . . ?
C21 C18 C28 O1 -168.9(6) . . . . ?
C21 C18 C28 C27 10.8(6) . . . . ?
C21 C18 C19 O2 176.8(5) . . . . ?
C21 C18 C19 O3 -4.5(6) . . . . ?
C21 C18 C11 C12 46.0(6) . . . . ?
C21 C18 C11 C6 -81.4(6) . . . . ?
C21 C22 C23 C24 -179.4(6) . . . . ?
C41 C42 C43 C44 -0.3(10) . . . . ?
C44 C45 C40 C39 178.1(6) . . . . ?
C44 C45 C40 C41 -3.7(10) . . . . ?
C34 C39 C40 C45 44.8(8) . . . . ?
C34 C39 C40 C41 -133.4(6) . . . . ?
C34 C39 C46 C56 164.5(5) . . . . ?
C34 C39 C46 C49 -79.9(6) . . . . ?
C34 C39 C46 C47 49.2(6) . . . . ?
C34 C35 C36 C37 0.1(9) . . . . ?
C51 C50 C49 C46 179.3(5) . . . . ?
C23 C22 C21 C18 -174.0(6) . . . . ?
C8 C9 C4 C5 0.1(8) . . . . ?
C8 C9 C4 C3 -178.3(6) . . . . ?
C8 C7 C6 C5 -0.3(9) . . . . ?
C8 C7 C6 C11 -176.8(6) . . . . ?
C12 C13 C14 C15 1.0(10) . . . . ?
C12 C11 C6 C5 -92.6(7) . . . . ?
C12 C11 C6 C7 83.6(7) . . . . ?
C12 C17 C16 C15 -1.7(11) . . . . ?
C25 C26 C27 C28 178.7(6) . . . . ?
C25 C26 C27 C22 -0.8(9) . . . . ?
C6 C11 C12 C13 24.3(8) . . . . ?
C6 C11 C12 C17 -155.4(6) . . . . ?
C30 C29 C38 C37 -2.3(9) . . . . ?
C36 C37 C38 C29 -177.8(6) . . . . ?
C3 C4 C5 C6 178.0(6) . . . . ?
C48 O6 C47 O7 -5.9(8) . . . . ?
C48 O6 C47 C46 172.9(5) . . . . ?
C38 C37 C36 C35 -178.7(6) . . . . ?
C38 C29 C30 C31 1.8(10) . . . . ?
C20 O3 C19 O2 -0.3(8) . . . . ?
C20 O3 C19 C18 -178.9(5) . . . . ?
